ArticleChemistry (Weinheim an der Bergstrasse, Germany)2021
Acetylenic Replacement of Albicidin's Methacrylamide Residue Circumvents Detrimental E/Z Photoisomerization and Preserves Antibacterial Activity.
Article in Chemistry (Weinheim an der Bergstrasse, Germany), 2021. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 7 papers.
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Who cites it
7 citing papers in PubMed, 11 citations in OpenAlex.
- Synthesis of Derivatives of the Antibiotic Albicidin: The N-Terminal Fragment as Key to Control Potency and Resistance Mediated by the Binding Protein AlbA.Chemistry (Weinheim an der Bergstrasse, Germany) · 2025Article
- Gene amplifications cause high-level resistance against albicidin in gram-negative bacteria.PLoS biology · 2023Article
- Transcription activation by the resistance protein AlbA as a tool to evaluate derivatives of the antibiotic albicidin.Chemical science · 2023Article
- Molecular mechanism of topoisomerase poisoning by the peptide antibiotic albicidin.Nature catalysis · 2023Article
- Optical Modulation of Antibiotic Resistance by Photoswitchable Cystobactamids.Chemistry (Weinheim an der Bergstrasse, Germany) · 2022Article
- Improvement of the antimicrobial potency, pharmacokinetic and pharmacodynamic properties of albicidin by incorporation of nitrogen atoms.Chemical science · 2021Article
- Acetylenic Replacement of Albicidin's Methacrylamide Residue Circumvents Detrimental E/Z Photoisomerization and Preserves Antibacterial Activity.Chemistry (Weinheim an der Bergstrasse, Germany) · 2021Article
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Authors and funding
8 authors at 1 institution in 1 country.
Funding
Abstract
The natural product albicidin is a highly potent inhibitor of bacterial DNA gyrase. Its outstanding activity, particularly against Gram-negative pathogens, qualifies it as a promising lead structure in the search for new antibacterial drugs. However, as we show here, the N-terminal cinnamoyl moiety of albicidin is susceptible to photochemical E/Z isomerization. Moreover, the newly formed Z isomer exhibits significantly reduced antibacterial activity, which hampers the development and biological evaluation of albicidin and potent derivatives thereof. Hence, we synthesized 13 different variants of albicidin in which the vulnerable para-coumaric acid moiety was replaced; this yielded photostable analogues. Biological activity assays revealed that diaryl alkyne analogues exhibited virtually undiminished antibacterial efficacy. This promising scaffold will therefore serve as a blueprint for the design of a potent albicidin-based drug.
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